(S)-2-Amino-2-(2-methoxyphenyl)acetic acid

Base Information

• Chemical Name: (S)-2-Amino-2-(2-methoxyphenyl)acetic acid
• CAS No.: 103889-86-7
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.191
• DSSTox Substance ID: DTXSID40908652
• Nikkaji Number: J1.626.149A
• Mol file: 103889-86-7.mol

Synonyms:103889-86-7;(S)-2-Amino-2-(2-methoxyphenyl)acetic acid;(2S)-2-amino-2-(2-methoxyphenyl)acetic acid;(S)-Amino-(2-methoxy-phenyl)-acetic acid;(2S)-2-azaniumyl-2-(2-methoxyphenyl)acetate;(S)-2-Methoxy-phenylglycine;(S)-2-METHOXYPHENYLGLYCINE;(S)-2-Amino-2-(2-methoxyphenyl)aceticacid;SCHEMBL12665837;2-METHOXY-L-PHENYLGLYCINE;DTXSID40908652;MFCD06858445;AKOS016843118;PS-12880;CS-0440092;Benzeneacetic acid, a-amino-2-methoxy-, (aS)-;(S)-2-Methoxy-phenylglycine (H-L-Phg(2-OMe)-OH)

Chemical Property of (S)-2-Amino-2-(2-methoxyphenyl)acetic acid

Chemical Property:

• Vapor Pressure: 2.6E-05mmHg at 25°C
• Refractive Index: 1.568
• Boiling Point: 343.9 °C at 760 mmHg
• Flash Point: 161.8 °C
• PSA: 72.55000
• Density: 1.246 g/cm³
• LogP: 1.47990
• Storage Temp.: 2-8°C
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 181.07389321
• Heavy Atom Count: 13
• Complexity: 184

Purity/Quality:

98%min ^*data from raw suppliers

(S)-Amino-(2-methoxy-phenyl)-aceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC=C1C(C(=O)O)N
• Isomeric SMILES: COC1=CC=CC=C1[C@@H](C(=O)O)N
• Uses: (S)-Amino-(2-methoxy-phenyl)-acetic Acid is a homochiral α-arylglycine that can be asymmetrically synthesized from substituted aryl trichloromethyl ketones and CBS-catecholborane reagent.

Technology Process of (S)-2-Amino-2-(2-methoxyphenyl)acetic acid

There total 13 articles about (S)-2-Amino-2-(2-methoxyphenyl)acetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

2-(benzylamino)-2-(2-methoxyphenyl)acetic acid (271583-23-4) → 2-amino-2-(2-methoxyphenyl)acetic acid (271583-17-6,103889-84-5,103889-86-7)

Guidance literature:

With sodium hydroxide; hydrazine hydrate; palladium on activated charcoal; In water; for 10h; Heating;

DOI:10.1080/00397910008087127

Reference yield: 55.0%

5-(2-methoxyphenyl)imidazolidine-2,4-dione (77651-54-8) → 2-amino-2-(2-methoxyphenyl)acetic acid (271583-17-6,103889-84-5,103889-86-7)

Guidance literature:

With potassium hydroxide; In water; for 60h; Reflux;

Reference yield: 18.0%

2-methoxy phenylglycine methyl ester (77651-55-9) → 2-amino-2-(2-methoxyphenyl)acetic acid (271583-17-6,103889-84-5,103889-86-7)

Guidance literature:

With potassium hydroxide; In water; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.joc.0c01302

upstream raw materials:

5-(2-methoxyphenyl)imidazolidine-2,4-dione

2-(benzylamino)-2-(2-methoxyphenyl)acetic acid

ortho-anisaldehyde

2-(benzylamino)-2-(2-methoxyphenyl)acetonitrile

Downstream raw materials:

methyl (+/-)-2-methoxy-α-<(thioxomethyl)amino>benzene acetate

(2-Methoxy-phenyl)-methylsulfanylmethyleneamino-acetic acid methyl ester

Refernces

• 1、 Inada, Haruki,Shibuya, Masatoshi,Yamamoto, Yoshihiko. "Synthesis of Unprotected 2-Arylglycines by Transamination of Arylglyoxylic Acids with 2-(2-Chlorophenyl)glycine". . p. 11047 - 11059. Retrieved 2020/10/12.
• 2、 Davies, Antony J.,Ashwood, Michael S.,Cottrell, Ian F.. "A facile synthesis of substituted phenylglycines". . p. 1095 - 1102. Retrieved 2007/10/03.